While living in Tucson, Bridwell worked with Mat Brooke and Jenn Ghetto, selling pizza. In 1997 the three moved to Olympia, Washington, but soon relocated to Seattle, where all three worked in a bar. Bridwell founded a record label, Brown Records, while Brooke and Ghetto formed the band Carissa's Wierd.[4] Bridwell later received some basic drumming tuition from Brooke[2] and subsequently replaced Carissa's Wierd drummer Robin Peringer, who left to play guitar on tour with Modest Mouse.[5] Bridwell later moved on to bass guitar.

Brown Records released the first two Carissa's Wierd albums, but Bridwell eventually gave up running the label and Carissa's Wierd released their third album on Sad Robot records, before splitting up in 2003.[4] The band reformed for a few shows in 2010 and 2011, but Bridwell took no part in that reunion.

Ben playing in Brooklyn on June 20, 2010 with drummer Creighton Barrett

Following the split of Carissa's Wierd, Brooke helped Bridwell learn to play guitar and he also began writing songs. He formed the band 'Horses' which soon had to change its name to Band of Horses, following the discovery that a long defunct band called Horses (featuring actor Don Johnson) were issuing re-releases.[2] Band of Horses were briefly a trio featuring Bridwell (vocals and guitar), Tim Meinig (drums) and Chris Early (bass), but former Carissa's Wierd leader Mat Brooke (guitar and vocals) was added to the line up and the quartet released their debut album Everything All the Time in March 2006. In response to Bridwell's success, Brooke said, " I kind of feel bad, maybe Carissa's Wierd was holding him back, all this time...(I am) extremely proud. He took the ball and ran with it. At a time when we were all down he picked himself up, higher than anyone thought he could. It's kind of like seeing your kid brother blossom."[2]

Brooke, Early and Meinig quit soon after Everything All the Time was released, but Bridwell recruited new musicians and the band's popularity continued to grow. Their second album, Cease to Begin was released in October 2007. It was recorded by the core trio of Bridwell, Creighton Barrett (drums) and Rob Hampton (guitar and bass), with keyboards by Ryan Monroe.

Band of Horses third album, Infinite Arms was released on May 18, 2010 and was nominated for a Grammy Award in the Best Alternative Album category.[6] For Infinite Arms the band became a five-piece featuring Bridwell, Barrett, Monroe, Tyler Ramsey (guitar) and Bill Reynolds (bass). That line up has also recorded the band's 4th album, Mirage Rock, which was released on September 18, 2012.[7]

Band of Horses third album, Infinite Arms, was released on Bridwell's previously defunct Brown Records label (along with Columbia and Fat Possum). Bridwell explained his original intentions for his label, "I really started it with the idea of it being a stepping stone. I would press a thousand CDs, we’d get ’em in stores...get in a local independent radio station and the band would have something to sell at shows and then hopefully a real label would pick it up. It got a lot busier than I ever imagined...in the end it just went out of control...I never expected it to be a real label. I’m re-pressing thousands and... ‘Shit, I’m...gonna have to do this correctly, people’s livelihoods (are) resting in my hands.’...I ended up cracking under the pressure, especially just getting those bands on a real label...That’s always been my calling, spreading the bands I liked that people hadn’t heard." With reference to the label's relaunch he added, "Now I’ve just heard that call again...a lot of artists are unheard that I think I can try to help with."[12]